Sodium Chloride → 2-(2-Nitrophenyl)pyridine

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1I)([O-:22])=[O:21].[Cl-].[Na+]>O1CCCC1>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N+:20]([O-:22])=[O:21]

Participants

Procedure

The reaction of 8.0 g (0.022 mole) of 2-tributylstannylpyridine with 4.92 g (0.020 mole) of ortho-nitroiodobenzene was carried out in the presence of 0.70 g (0.001 mole) of dichlorobis(triphenlylphosphine)palladium in 100 ml of tetrahydrofuran at 110° C. After 24 hours from the start of the reaction, a saturated aqueous sodium chloride solution was added to the reaction mixture and the reaction product was extracted with ether. The ether layer was then washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The resulting liquid was purified by column chromatography and concentrated to give 0.96 g (0.0048 mole, 24.9%) of ortho-(2-pyridyl)nitrobenzene as brown liquid.